Sodium allylsulfinate | 106181-88-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: Sodium allylsulfinate
• 英文别名: Sodium prop-2-ene-1-sulfinate；sodium;prop-2-ene-1-sulfinate
• CAS: 106181-88-8
• 化学式: C₃H₅O₂S*Na
• 分子量: 128.127
• InChiKey: YEWHYKOQJJHRFI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.94
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4'-二溴苯乙酮 、 Sodium allylsulfinate 以 甲醇 为溶剂， 反应 5.0h， 以92%的产率得到Allyl p-bromophenacyl sulfone
  参考文献：
  名称：

  Desulfination of Allylic Sulfinic Acids: Characterization of a Retro-Ene Transition State

  摘要：

  Allylic sulfinic acids have been prepared by cleavage of trialkyltin allylic sulfinates with trifluoroacetic acid (TFA). Allylsulfinic acid prepared in this way could be trapped as the sodium salt or observed by NMR and UV spectroscopy to undergo spontaneous decomposition to propene and sulfur dioxide at ambient temperatures. The corresponding reaction of 1-methylprop-2-enylsulfinic acid was regiospecific, yielding (E)- and (Z)-2-butene (E:Z = 82:18). Acidolysis of E/Z mixtures of trimethyltin 5-methylcyclohex-2-enylsulfinate with [H-2]-TFA followed by desulfination indicated that the latter process proceeded with gamma-syn deuterium migration, consistent with a concerted, retro-ene mechanism. A detailed kinetic investigation of allylsulfinic acid desulfination supported this conclusion. This reaction obeyed a first order rate law (k(297K) = (5.5 +/- 0.1) x 10(-4) s(-1) in toluene) with a large, negative activation entropy (Delta S double dagger = -146 +/- 17 J K-1). The rate of desulfination was essentially independent of solvent. The volume profile (Delta V double dagger = -5.5 +/- 1.0 cm(3) mol(-1), Delta V = 15 +/- 5 cm(3) mol(-1)) is comparable to that of a retro Diels-Alder reaction and taken together with the above evidence and a relatively small deuterium kinetic isotope effect (k(H)/k(D) = 2.5 +/- 0.1) strongly supports a concerted desulfination, proceeding via a relatively compact, early transition state.

  DOI：

  10.1021/jo00127a022

文献信息

• <b>Preparation and Reactions of 1,2-Dicyano-1,2-disulfonylethylenes</b>
  作者：E. L. Martin

  DOI：10.1021/ja00899a025

  日期：1963.8